Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 14-15, Pages 2538-2548Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000383
Keywords
2-arylsulfanyl-arylcyanamides; cascade reactions; copper catalysis; ligand role; one-pot reaction
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Funding
- DST New Delhi [SR/S1/OC-79/2009]
- CSIR [01(2270)/08/EMR-II]
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We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl-arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).
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